



Patented Aug. 17,1948 1 I I 2,447,116 amma COMPOUNDS Adolfz'Griimideceasedtlatc of Basel, Switzerland, byg-Franz -Griin administrator, Basel, Switzerland, assignortolILR. Geig -At G Basel, Swit ."zerland v I No Drawing. Application Fbj'naryi'1 S48, Se-- I rial No. 7,292. In Swi-tierland AbriliZE19391-1 The; present. application iiseconcernedi more te r C. The.solutionis-filtered off}. from thel lsalt particularlmiwith .th'ose; triazinoscompoundsawel residueeandrconcentrated H -V Q, T iy substituted guanamines) which havingcthez'folz-r ing;product;iis fi carbcxytpr 91 ???-g tilamme lowinggformulazi v I I sCLCHFCHkOOOHfi,

5. in which R. is a carboxypolymethylene radical NH, and G is ,a guanamino radical.- having a free .,4 valence on the carbon atom of the triazino ring which does not have an" amino group attached 1o to itathe bond between RF and -G bein-ga -ca-rbom and 1S clilisstandmmslblmI tot'carbon' bond? Illustrativecompounds ofi tliis g rl g. character are inter alia the following: p-ear=- To 353parts qffibiguanide dissqlvedm 5 parts boxypropionoguanamine, w-carboxy pelargonot fi fhafibl' ht jnjfigflfizfparts offsodium uan mi a h methcsxine e1addd462partsofsodiummethyl The mventlon 15 b upon the observation succiziate'i' Thisreacti'on'mixtiire wasstirredfor that, contrary to expectations in view of the prior about day even though precipitation apart experiences with this type of compound, it is eared to be completed in about five to six hours. possible to obtain the aforesaid Z-substituted The insoluble product was removed by filtration guanamines, which may also be regarded as 0 and the methanol was concentrated to yield fur- 2:4 diamino 1:3:5-tr1azino compounds, very ther product. s crude sodium pwarboxyprm readily and in smooth manner by the reaction pionoguanamme amounting t bo t 425 parts under suitable conditions between biguanide and was dissolved in t fiu d i der to rethe Corresponding Carboxylic acid halide- In this move the small amount of insoluble material and connection: it is preferred to carry o the r then acidified to a pH of about 4.0. The precipiaction in a medium containing a non-caustic tated 5.carboxypropionoguanamme acid-binding agent.

The compounds of the present invention may serve as intermediate products for the manufacture of medicinal and therapeutic substances 3o a g and dyestuffs, as well as textile assistants, softening agents, etc. N

T present application m part commw was filtered, washed with a large volume of water atlon of copenchng apphcation S. N. 434,624, filed d th d t C The 161d of colorless March 13, 1942, and entitled Manufacture of an a d 3 y t 2:4-diamino-1:3:5-triazines, now Patent No. and mfuslble pro uct was 32 par 2,437,691, issued March 16, 1948. The appended Example 3 i correspond to claims respec 209 parts of ethyl succinate were added to 101 uvely' p' i apphcatlon' parts of biguanide dissolved in 400 parts of warm The mventm 1s Illustrated but mt limltedt 40 methanol. Within a few minutes the product fouwgng fi f g. i g being by began to precipitate from the solution and after Welg t excep as O erwlse m e standing overnight the product was filtered and Example 1' washed with methanol. This material was then extracted with about 300 parts of hot ethanol, which dissolved the ,B-carbomethoxypropiono- 11 parts of biguanide are dissolved in 400 parts of toluene, 12 parts of anhydrous soda (sodium carbonate) are added and gradually combined, guan'amme while stirring at -6'0" C., with 15 parts of ,B- 2)2 OOCHa carbomethoxy propionyl chloride dissolved in the same quantity of toluene. The temperature is so L IJ raised gradually to and then maintained for 16 2 hours at 0., after which it is allowed to drop N melting at 159 C. The residue left from the alcohol extraction was succinoguanamine melting about 335 0., which could be further purified by dissolving in warm dilute hydro-f chloric acid solution, followed by precipitation with ammonium hydroxide.

When the amount of biguanide was doubled the succinoguanamin'e was obtained in about 75% yield and the mono guanamine was absent.

Example 4 of biguanide are dissolved in 400 parts 12 parts of anhydrous soda (sodium 11 parts of toluene,

carbonate) are added and gradually ,combined, ,2

while stirring at ESQ-60 C., with 22 parts of w-u 5 f ing at 223-225 was 75%.

carbomethoxypelargonyl chloride dissolved in the v same quantity of toluene. raised gradually to and then maintained for 16 hours at 110 C., after which it is allowed to drop to 80 C. The solution is filtered oif from the salt residue and concentrated in vacuo. The resulting product is w-carboxypelargonoguanamine o-wnmooon N v N H2N-JJ\ NH2 and has a melting point of 223-225 C.

Example 100parts of biguanide were added to 280 parts of sodium butyl sebacate dispersed in about 1200 parts of methanol warmed to about 55-60 C.

The temperature is' The reaction mixture was stirred at room temperature for about 24 hours. After filtering and washing with methanol, the sodium salt was dissolved in about 2500 parts of water, and filtered hot. The filtrate was acidified to a pH of about 4.0 and the precipitated w-carboxypelargonoguanamine o 0m)|co OH Y was extracted with alcohol in order to remove any sebacic acid. The yield of purified product melt- 1 Having thus disclosed the invention, what is claimed is:

in which R is a carboxy polymethylene radical, the bond between R and C being carbon to carbon bond. 1 r

- V FRANZ GRI'JN, 7 Administrator of the Estate of Adolf Grim, De-

ceased. 

